The Vine: January 30, 2013

How do you push yourself into having sex if your body/gut instinct doesn’t necessarily want to? I know from reading previous columns that you’re normally a fan of “getting it over with” with a good-enough candidate rather than waiting for a perfect moment.

Logically and rationally, I would like to experience sex, even boring or bad sex, but I have reservations about it. And no, I’m not 19 or 25, I’m 36 with no particular sexual or relationship experience. I am the worst result of what happens if you tell twenty-somethings to hang in there and be open to possibilities because eventually it will happen (which is what I thought in my 20s and I believed it then, too). I didn’t worry about it much at all, and then I hit 29, my father got sick and died, and I spent the next few years too depressed and sad to worry about sex. I then headed to graduate school and had two years of really being happy and having friends who loved me…however, I hit my 36th birthday and my mother was suddenly horrified and negative about my advanced age. (She’d like grandchildren, I don’t care.)

I’m also away from said friends and have a pretty unhappy and lonely life at the moment, which is adding to the problem of obsessive anxiety and sudden worry about the issue. I am working on fixing the life, so that part isn’t a problem. However, since most of my friends are partnered or parents, and the single ones have at least had some experience, I’m feeling like the isolated, lonely adult who thinks there is something wrong or broken about me. I usually make up some vague stories, depending on who the friends or dates are, to cover my abnormality or freakishness, but it’s always anxiety-provoking once the subject turns to sex and I can’t relax about sexual jokes in case I give something away.

I am fully aware of all the Google results about adult virginity and how the farther above 30 you are, the “weirder” you are, and how you can’t develop as a sexual person if you’re waiting for the perfect partner, etc. I was waiting to feel real attraction, but I don’t think that will happen in my case. There are all kinds of reassuring stories from 20-somethings who lost their virginity late, and occasionally even stories from people over 30; I’ve just never seen someone at my age trying to negotiate sex. I don’t plan to mention it at all – enough reading has convinced me that I shouldn’t trust anyone to be kind about this, whether potential partners, feminists or anyone else. My good-enough candidate is okay but not someone I’m attracted to or like or think about very much, even though we’ve been on 4 or 5 dates.

I think I’m wired backwards – I’m around men for a few months, gradually develop feelings for them, and then sexual attraction is the very last thing that happens. I’m not visual at all, and it can take anywhere from a few months to nearly a year to get attracted to someone as in the really lustful, sweep-you-off-your-feet kinds of feelings. The other problem is that I’ve only been attracted to about eight men in the twenty years or so since puberty – a timetable of roughly every two years, only since the age of 28, it’s been every four years. The last two men have been attractive both emotionally, intellectually and sexually, which was a first, but didn’t return the feelings.

There’s not a lot out there about what to do when your crushes just aren’t requited, besides move on – and after a certain point, most people seem to assume you’re asexual or you just haven’t felt sexual desire. And a few men have liked me (even though I didn’t figure out I was attractive until about 23 or so), but as bad luck would have it, I didn’t like them back. Sometimes I wonder if I shouldn’t have just slept with the guy who offered when I was 26, but I wasn’t attracted to him, so I said no (a few make-out sessions in college felt a lot like breast exams at the gynecologist’s, and that’s kind of what I’m guessing sex would be like).

I actually have a pretty normal sex drive, just very little ability to want to sleep with a lot of people, and I think there’s an assumption that interest in sex = wanting a lot of partners or thinking one partner is as good as another. (My therapist does not seem to think that there’s Something Wrong with me.)

Now, I’ve rather given up on sex with mutual attraction or mutual love, so I’m wondering how bad boring or “getting it over with” sex can possibly be. I’m of two minds about it: it feels like I’d at least feel a little more normal to learn that there is no “secret,” and maybe it would open the door eventually to some sort of companionship. I’m not upset about being single forever since I do have friends who love me, and I do realize that true loneliness is dating someone you don’t like and having to pretend it’s love.

But I would also feel like I’d be doing it only to feel normal, plus I’d have to be drunk or think of it like sex work in order to be able to get through it. What say you and the TN readers?

Conflicted

Dear Flick,

A couple of things jump out at me here, starting with this: “a few make-out sessions in college felt a lot like breast exams at the gynecologist’s.” I had many make-out sessions in college, and most of them felt like that, and/or like being greeted by an enthusiastic retriever. College dudes oftentimes just aren’t very good at making out (not that college gals are either, necessarily; I was hardly Dance of the Seven Whatevers myself, but you know what I mean), so that isn’t the greatest evidence for a “the first time is something to be endured” platform.

On the other hand, there’s this: “I’m wondering how bad boring or ‘getting it over with’ sex can possibly be.” Um: it can be pretty bad, I won’t lie. The first time with any partner is a bit awkward; not always, but a lot of the time it’s elbows, and having to turn a too-bright light on to deal with the condom wrapper, and “Could you move up a little bit? …Your other ‘up’?” And the very first time is painful for some women, plus you’re anxious, which doesn’t help you relax down there…a lot of people report that their first time was magical. A lot more people are mostly glad it’s done with.

Not to give you more agita here, but…how to put this. Okay: it’s not exactly a secret that a woman’s first time is often uncomfortable. This is a big part of why I recommend getting it over with; the unknown is the biggest obstacle, and once you know what it is, you don’t have to fear it (plus a major part of the fear, the pain, is probably over with). But I get the sense that you’re looking for reasons not to do it — reassurance that it’s okay to find it daunting, or off-putting, or not a priority, or the validity of any of those rationales.

And if you don’t want to do it, that is fine. “I would also feel like I’d be doing it only to feel normal.” You and almost everyone else on earth, who had no way of knowing whether we were “ready” until we did it, who didn’t want to get left behind (I skipped a grade, I had myriad issues with that). That is fine. “I think I’m wired backwards” — join the club. I’ve had a few partners I didn’t develop a truly deep attraction to until we had sex. It happens. Everyone’s different, there’s basically no “normal,” and that is fine.

If you want to wait some more, wait some more; if you want to strap your pinot on and get it over with with the first likely sailor who comes to port, do that. I would advise you to do it, because you say you understand that it can’t be perfect, but I don’t think you really do. You can’t; you’ve never done it. This is not a judgment, but whatever you think about sex and whatever you think other people think about sex, before you’ve had sex, it’s just passing the time; you have no context.

Again, that’s normal. I did the same thing. It’s a way of controlling a situation that seems very fraught and chaotic (and can be); I don’t think you’re having any inappropriate reactions. But I do think it’s better to do it, and have done it, and maybe have a few things you’d do differently the next time, than to have to keep thinking about it. Your virginity is making you unhappy and taking up too much psychic real estate. You deserve not to have to think about this anymore, because I don’t think there’s any way for you to think about it at this point that doesn’t make you feel alienated and freakish — about what’s essentially bad timing, and not a comment on you at all.

For your own sake, enough. Try it. Understand that it is what it is the first time, but also let yourself be a drama queen about it, a little bit, because it’s a first and it’s intense. (It can also be hilarious. The design of the human penis is puzzling. No offense, penis-havers. Love you guys. I’ve totally lost control of this parenthetical. [kaff] Anyone here from Jersey?) Everyone has Things Around It; accept that and give yourself a break.

And if you don’t try it, the only one who’s going to be disappointed and think you’re all busted and fucked up is you. You aren’t. And the Nation probably has some citizens who were a little…less eager than I? More considered? Waited longer, in any case, and can speak to your situation a bit more directly, so we’ll hear from them.

Short verzh: Do whatever you feel, but in my opinion, you will feel better if/when you have done it.

74 Comments »

I jumped into sexual things right at the start of college, because I thought that’s what I wanted, and I was wrong, and I was lucky the second person I hooked up with was my husband because then love overtook all the crappy sex we were having. There’s definitely no particular merit to having sex at any time before you’re ready.

That said, the guy I was with before him was actually better in bed, but I didn’t like him or feel comfortable with him so it didn’t matter. So there is some merit to having sex with a person you like, whether it’s good or not, because it’s not necessarily the sex you’ll be having forever (our sex life, 13 years later, is perfectly fine). On the flip side, though, I’m glad I started with the guy who gave me the creeps, because it got me over the anxious hurdle and into feeling like sex was just an activity, not some huge Thing, and that it could be bad and I could live through it and dump the guy and move on.

In Conflicted’s letter I notice a lot of assumptions, both about how the world works and about how other people think, which might or might not be true but will absolutely keep her from doing the things she wants if she believes they are true. I recognize this stuff as the kind of rationalizations I make when I’ve already mostly talked myself out of doing something I actually desperately want but don’t have the confidence for (“Well, nobody ever gets a job there and the neighborhood is bad and people don’t like out of towners so I won’t move there”). I would urge her to just ignore the fuck out of the voice in her brain that keeps generating this stuff to stop her from doing something that might be scary or difficult, and if she puts it like that to her therapist (“help me turn off my inner critic”) I bet said therapist will have some ideas on changing that behavior.

Your virginity is making you unhappy and taking up too much psychic real estate
————–

This. A hundred times this. You have overthought this to the point where no experience around it will be all that great. I normally am a proponent of having sex when you are ready to have sex and want to have sex (no fourth date or engagement or bathroom-on-the-first-date guidelines needed), but in your case, you have built up your virginity into a Thing That Makes You Weird, and while I DON’T think being a virgin late in life is weird unto itself, it doesn’t have to be that way. So, get rid of it. If you are asking these questions, you are ready to have sex. Let it be so.

I also might suggest separating “losing your virginity” from “enjoying sex.” As Sars noted, the first time with a new partner usually is a little weird, and the very first time isn’t that great for most women. BUT they both get better, and getting over the hurdle of the first time(s) is well worth it for the rewards that come later. The discomfort the first time wasn’t something that gave me nightmares or PTSD or anything; it was a little uncomfortable at first, but I didn’t need to, like, take 3 Advil afterward. Having my wisdom teeth pulled was WAAAAAAAY worse.

Mostly, the whole thing was a “Huh. So THAT was it?”

It’s now several years later, and after that first anticlimatic (heh!) time, sex is a good thing (although I’m single and don’t get to have it all that often). So, really, if you have someone in your life that you like well enough and who wants to have sex with you, please, go have sex with them. Have your own “Huh. So THAT was it?” moment, and move on with your life.

(I also would tack on: some dudes just aren’t that skilled (which is a drama unto itself. Whole TV shows and books and seminars exist on this topic), AND some women just aren’t sensitive in certain places. If you didn’t feel tinglies being touched in one place, that is normal; you just might not have had anyone hit the place where you DO feel tinglies.)

You know, my first time was with someone who didn’t love me back as I loved him. I figured it was “good enough” that I loved him and that it was time to get “it” over with. It was a bittersweet sort of goodbye thing. Non-mutuality isn’t the worst thing if the other person is kind and considerate and gentle and patient. I look back on the experience with fondness. Was it ideal or everything I’d hoped for? No. But that’s OK. So if there’s someone you care about who isn’t necessarily in love or interested in a long-term relationship with you, but who would treat you well in a sort of short-but-sweet kind of way — or maybe someone entirely impractical, you know, like a man who’s moving far away soon to somewhere you would never follow, a soldier about to be posted overseas, say? — it can be poignant and even kind of lovely, especially if you have some feelings for him, however unrequited.

I could’ve written this letter, except minus any experience of anything in college or since. I had my first and last kiss at 27. I feel completely normal in most other aspects of my life but I really feel like I’ve missed the boat and there is no way to swim out to it at this point. All my friends are married/in relationships (to the point where they’re getting the baby-making parts turned off because they’re done in that area of their lives), I’ve never been on a date, I’ve never had the chance to say no or yes. I have a lot of guy friends, but it’s come to light that a lot of them thought I was either gay or saw me as “one of the guys.” (I mean, I will take trips with my married guy friends where I’m the only female and their wives couldn’t care less.)

I’ve talked about this with several therapists and while they are supportive, they’ve both basically said, “you may be a rare case where the opportunity never presents itself.”

So that’s encouraging. I don’t know if I feel better or worse for knowing there is another 36 year old virgin out there that feels very weird about the whole situation, only because she’s had opportunities and turned them down and I haven’t even gotten that far.

I had the “getting it over with” sex for the first time, with a one night stand that I picked up at the bar and never saw again. Granted I had just turned 22, so I don’t have the experience of being older and dealing with this.

But like you, I had grown quite fixated in a negative way on my virginity. My experience was obviously my own, but I can tell you that things got a LOT better once I got the experience out of the way.

It was only a little bit uncomfortable (it helped that I was slightly drunk, and therefore a little more relaxed). I didn’t mention I was a virgin because I didn’t want him to freak out and stop. It was mostly just exciting, because I had NEVER done anything like that before.

After it was done, I just felt so relaxed about sex. I started having more confidence with guys I met, and frankly went through a bit of a “slutty phase” that many get out of their systems in college, but hey, I was a late bloomer.

And I don’t regret any of it, and I think going through that phase helped to open me up socially and made me able to meet my first real boyfriend at 24, and my husband at 29.

Kind of out there idea – maybe you should find an escort service for your first time. I wouldn’t suggest it except you seem to have a business like attitude about losing your virginity as opposed to a fairy tale scenario desire.

Reasons:
I don’t think it’s a good idea to have sex without telling your partner you’re a virgin – it isn’t fair to them. Plus, I could see how doing that would make you more anxious. An escort has probably seen lots of weird stuff (including older virgins) and probably won’t care.

an escort’s job is to be focused on you, not them. This should reduce the awkward that can happen your first time (and I mean first time with anyone, not first time ever. There’s always some awkwardness the first time). He’ll be attentive and attuned to you and that should make it better.

you won’t have to see him again, so if you feel awkward or embarrassed, no big deal. If it’s someone you are planning on having some kind of relationship with, that ups the pressure, especially if it doesn’t turn out well.

Ideally (and maybe I have an unrealistic idea of escorts), he’ll know what he’s doing and will have dealt with different types of women/situations.

I’m in a very similar situation, and I’m glad to hear from someone else. I just don’t want to have sex with anyone I don’t love, and I’ve never been in love. I certainly hope that changes, and I think Sars’ advice is great.

I was a late bloomer myself, lost it at 25. And it was great. It was incredibly difficult beforehand, for all of the old virgin reasons you totally already know: feeling left out, feeling like you have this dark secret, feeling vulnerable. But I kept away from dudes for a long time because I had body issues and trust issues and just general issues to spare. When I finally started feeling ready, there was this great guy who was interested, and even though I didn’t TELL him “I have no experience in anything,” it didn’t take him very long to NOTICE I didn’t have experience in anything, and he brought it up so I didn’t have to, and he was cool with it, and he made me feel cool with it. And by the time we were ready to do it, we were so comfortable with each other and falling in love (plus by that age I had my own apartment so there were no logistics of “where do we do it?” which is a major bonus to the old virgin thing) that it was really a great experience.

I would disagree about doing it just to do it, though, I think. Because of that difficult virgin period, sex had this bad connotation for me, this “too cool for me” “too big for me” “too scary for me” thing, and if I had tackled it like some disagreeable task, I feel like I never would have been able to grow into finding it something positive. I certainly would not have motivated to keep plugging away at it. So then why do it at all?

But the problem here is that everybody’s experiences are so different, everybody does it too soon or too late, or with too many people or too few people, and nobody can say which path is the right one except for you. So just do what feels right to you, be kind and demand kindness in return, and use protection, and you should be fine.

My first time was in college, but it was just because i was sick of worrying so much about the “should I/Shouldn’t I” ALL the time. It wasn’t great; it wasn’t awful. But at least i could quit worrying, questioning, wondering. It is now decades since college and i feel it was the right decision, at least for me. ( just my 2 cents worth)

I had my first time way later than I intended. I tried with three separate guys I actually cared about before it actually happened and each time the guy had “performance issues” for various reasons (my friends started accusing me of having a gypsy curse).

So one night, I met a guy in a bar and later that week he called me late at night and I went over to his place and got rid of my virginity. The sex was a little painful and the guy was, in retrospect, a very selfish lover. I would not say we were sexually compatible. I left the next morning and my first thought was “God, I hope he doesn’t call me.” He did and I blew him off.

So, sex: not great. Guy: not great. But, it was such a relief to get it over with. Like the LW, I think I let my virginity occupy my thoughts to an unhealthy extent. Since then, I’ve had sex of varying levels of enjoyment. I’m glad I got it over with. I was adult enough to not let bad sex affect my identity or perceptions of the world. I think the LW would be the same.

Also, LW, aren’t you curious? About what sex is like? In a way where it doesn’t matter if you really like the guy? Maybe think of it as having sex for sex’s sake instead of for the guy?

Good luck. You are certainly not alone and I agree with Sars 100%. Better to get it over with.

I am 32 years old. I lost my virginity last Thursday. I had definitely been worried and scared about it. I was also feeling so much pressure to do it. I thought something was wrong with me because I was the only one I know who hadn’t had sex. Now that it’s done, I realize I was putting way too much pressure on myself. I was worried it would hurt or I’d do something wrong and get laughed at. I came really close to having sex a few years back and panicked when it came time to take off my pants. Looking back, I know that I just wasn’t ready, even though I thought I was. Fortunately, it happened with someone I’ve known for a while who was in town, visiting me. It wasn’t amazing but it wasn’t horrible. I was lucky, I know, because she did everything she could to make me comfortable and didn’t laugh when I asked questions. I guess my point is you’re not alone. Try not to put so much pressure on yourself.

I have been enjoying this blog lately called “The Dirty Normal.” The author is a health/sex educator at a women’s college. I have found reading the blog very useful for learning how to think of my own sexuality/sexual experience as normal instead of weird. (I am a 28 year old who has never had sex. Before you go thinking, “well, but 28 isn’t 36,” let me just add that I am a 28 year old who has never so much as kissed a partner. So, like, I get how hard it is to not feel like a freak of nature and totally behind all your peers.)

One thing you could consider: She talks about is how some people, particularly women, have “responsive desire” as opposed to “spontaneous desire”. They think of themselves as having an abnormally low sex drive, because they’re seldom interested in initiating sexual activity. There’s an entry about it here. You highlighted the fact that there’ve been very few men you’ve felt a desire to be sexual with. Maybe you’re more of a responsive-desire type, and if you start down the road of being sexual with someone you’re willing to have sex with, even if you’re not that enthusiastic about it, the desire will kick in. Maybe not. Who knows?

Oh, one other thing: I imagine you’ve already thought of this, because you appear to have thought this issue through very thoroughly, but if you want to lie to your partner about your previous sexual experience, you can still come up with a like that feels truthful. Something along the lines of, “I’ve been dealing with my mother’s death and then the start of grad school, and relationships haven’t been a priority for me for a few years, so I haven’t done this in a while.”

I am in exactly the same boat. I’m 33, just kept waiting to meet someone that I wanted to date and would date me, then didn’t care for a few years after my Dad died, then did care but haven’t found anyone yet. I felt like a freak for being a virgin until I was about 31, then I suddenly realized that it didn’t bother me anymore. I just wanted you to know that you are not alone and it is possible to be ok with it while still wanting it to just freaking happen already.

I think you need to ask yourself if you do it, what are you expecting to change in your life, and is that expectation practical? Is being a virgin holding you back from dating or being more outgoing or pursuing guys you like? Do you think doing it is going to change that? I mean those questions honestly. Is your feeling that you are abnormal holding you back? If the answer is yes, then hell yes, just do it so you can stop feeling that way and move on with your life. But if the answer is no, you’ll be having sex with a guy you don’t even like just to check it off the list, so why bother? Three of my friends went the “do it just to get it out of the way” route and none seemed all that excited about it, or even relieved not to have the label anymore. Just meh. So manage your expectations.

I don’t feel like a guy comes along in my life very often that I’m interested in or that’s interested in me, so when that happens, I feel like I have to take advantage or the opportunity might not come up for another few years. I don’t know if that’s how you’re feeling right now, but I don’t think that having sex is going to change that. Someone will come along or you’ll find them (or you won’t, who knows) whether you’ve had sex or not. I don’t think having sex, just on its own, is going to increase the number of potential mates that come into your life.

If you can figure out a way to not feel weird because you’re still a virgin, then I don’t think you should have sex with this guy. But if you don’t see that happening, then Sars advice is probably more useful.

Yikes. I could have written this letter. I was a late-blooming virgin who decided to get it over with one-night-stand style. I think that approach worked well because while we had a fun night, it was still awkward and I think it was ultimately better that we would never see each other again.

The one thing I empathize with Conflicted to no end about is the gradual development of attraction. I don’t know whether it’s the impatience instilled in us by the Internet Age or what, but many of the men I’ve dated want that instant “click” within the first two dates or they’re gone. Whereas it takes me longer (sometimes MUCH longer) to figure out whether I’m interested in someone. That’s why I don’t need my toes to count the number of crushes I’ve had in my lifetime. Trust me, YOU’RE NOT ALONE.

I too am attracted to personality and intellect first, body second. So when a guy wants to get physical right away, it feels really weird to me and doesn’t (usually) endear them to me. There’s really no greater turnoff to me than someone who isn’t interested in the whole package (there’s a brain that goes with these boobs, fellas).

Dating is especially frustrating for us gradual-attraction folks, because no one seems to want to invest the time it takes to get to know us. That’s why I thoroughly recommend doing MeetUp groups, book clubs, classes at an Art Center, or whatever hobby floats your boat. That way you’re meeting men who share your interests and you get to see them once a week, once a month, or however often the club meets. The trick is, I found, is that you have to resist the urge to have a super-secret crush forever and ever. If you’re attracted to a single guy (even if it hasn’t developed into sexual attraction yet), ask him out and see where it goes.

I also highly recommend exploring your sexual interests on your own. Knowing more about your sexual preferences tends to reduce anxiety about “the first time” and may (I emphasis may) make it less awkward for you and your partner. Some books to read: Moregasm published by Babeland, and Getting Off by Jayme Waxman. And if you’re not reading Dan Savage’s Savage Love column, I thoroughly recommend that as well.

OH GOD THIS. I felt that way, and I was 17. I think everyone feels that way. I STILL feel that way sometimes. It’s very unlikely, and if it DOES happen, the guy is all of the assholes, but it’s totally common and totally legit.

Just saying, you’re not alone in this. I’m almost 32 and no progress on this front either. It just didn’t happen in my 20s (I never met someone I liked who liked me back at the same time) and then my health went haywire and now it’s like “well crap.”

I don’t have suggestions or a plan, just wanted to offer some support.

I’m going to throw it out there, although obviously I don’t know you and it could be in left field-are you SURE it’s a man you want to lose it with? Because the way you talk about not a visual person? No attraction to anyone, not even purely physical, that you haven’t known for at least a few months? Really attracted to only eight men in twenty years?

I’m not saying this to be unkind, and I know that women are generally less visual than men. But still-Hugh Jackman doesn’t do anything for you?

If I were devising your plan, I’d start with frequent massages by a good, professional masseur. They’re great, so you won’t regret them no matter how you proceed. And there you are, naked with a man touching you non-sexually. That’s one facet of the experience, already learned and processed.

Do you like your body?

I am pretty damn sure that straight grown men will like your body as much or more than you do. So if you don’t like it, and you hide it in covers or dark, that’ll be their starting point, and then they’ll like it more than that because straight men like women’s bodies. But if you LOVE your body, they will start from there and catch your confidence and joy. You can set the stage for that by liking your own body. You can work on that by being aware of the way it carries you, how it feels moving and breathing, by being naked and enjoying the sensation; by doing sensual things with awareness. (Basically, don’t be a mind on a stick.)

I probably have more advice, but while you are figuring out how you want to handle the rest, you could do those things and they’ll be enjoyable no matter what.

I was someone who didn’t come into my own until after University and was out in the professional world. So, of course, by this time all of my friends were in relationships and having lots of sex. I would obsess about dying a lonely virgin and even the thought of dating scared me because it seemed hard enough to date without worring about how I was going to explain why I was a virgin as well.
I slimmed down a bit, started paying a bit more attention to my clothes and hairstyle (now that I had disposable income)and just generally felt better about myself. I let friends set me up on blind dates and my first time was with a guy I went on a few dates with, he was nice enough but I wasn’t overly physically attracted to him. The sex was pretty forgettable, it was slightly uncomfortable (and I went into the whole thing with my drama queen best friend’s voice in my head telling me about her first time, The Blood!! The Pain!!) but no mess and I didn’t tell him I was a virgin. We actually dated for several months and I still look back at the experience fondly because it made me realize that sex is only a big deal when we make it one. I had fun with him, learned some moves, and found out what I liked and didn’t like. My next blind date was with the man I ended up marrying and I have never regretted not waiting for “the one”. Don’t let sex become SEX,and I found that when I stopped obsessing over it dating and relationships just fell into place more naturally.

Leave it to the nation to make me feel more normal. Thanks previous commenters!

Finally a vine where I feel like I can really weigh in. I “lost” mine just over a year ago, when I was 35, and thought that was horribly old. I had a lot of baggage and religious guilt from being raised with the “good girls don’t” thing, but even after I got past that, I just wasn’t ready. I’m different from the LW in that I went right up to the doorstep for years but couldn’t bring myself to take that last step, so I had some experience with at least some of it. I wasn’t ready, and if I had pushed myself, I think I would feel awful about it. And as mocked as it is to wait as long as some of us have, there is something to be said for being ready. I decided I was ready when I was 32ish, and it took me a while to find the right guy. It sounds like you, LW, might be ready.

I met my guy on craigslist via a “friends with benefits” ad. I know that’s frowned upon as “dangerous” in some areas, but we met for the first time in a public place, and talked for hours before heading to my place. The sexxin didn’t happen til a week later, but I was comfortable with him right away, and when it came out that first night that I was technically a virgin, we both knew it’d be him. LW, I would urge you to tell whoever it is. I think my guy tried extra hard because he knew. Maybe I was just really lucky, but I can honestly say that it was awesome for me. It didn’t hurt at all, I was ready, he was caring, and we worked together to make it good. He was never my boyfriend, there was never love involved, but we liked each other, had fun together a few times, then we both moved on, and that was ok.

So my advice? Find the person you think you might want to try it with, and be honest. It might be sucky and awkward, but you can use his reaction to gauge whether or not he’s the right one. The right one might be surprised, but he’ll want to do right by you. Good luck.

The first time I had sex was with my husband, who was also a virgin. I was 21, he was 30. The sensation of having something “there” was a little weird, but not unpleasant. So very glad I didn’t do it with someone random, or really anyone else. I feel very emotional and vulnerable after sex and can’t imagine opening myself up that way to a stranger or acquaintance. Something to consider is that no form of birth control is 100% — you could conceive a child with Mr. First Time. Honestly, I would watch lots of sexy movies (not necessarily X-rated) and have fun alone until you meet someone you really care about.

Megan’s got it going on here, take her advice! Especially about the massage prelude. Think of it as a non-Jewish mikvah bath, something you do to make a body ritual with which to get your head in the game.

To me the only tricky part is the lucky fella (if you do indeed want a man). I wouldn’t like to see you go off with a pickup who is dangerous, or someone who won’t use a condom. I want to rule strangers out for that reason, that’s just me. Best case scenario would be a Big Chill where somebody lends you her man for the night, but it’s nothing but a plot twist. Unforch.

Is there anybody you know who could channel Jimmy Buffet and, just get drunk and screw?

Twenty years old, with a one night stand. I had tried to lose it earlier with a friend I was totally into, but when push came to shove (heh), he’s the one who just couldn’t go through with it. Too bad–it’s weird, I was just thinking of him this morning and fondly remembering The Dick That Got Away (Hey, X! You were awesome and not a dick, you just had one, if you see what I mean okay I’ll shut up now.)

But anyway, I think one aspect of your thinking that’s making it difficult for you is the idea that any sort of difficulty will render you a Failure At The Sex. Difficulty is just part of that vast area we call normal, not some kind of scarlet marker branding you as wacky, weird, or not worth it (all of which are completely false brandings.)

Sex can wear many trappings–act of love, act of lust, personal milestone–but in the end it’s a biological function that feels anywhere on the scale from “meh” to “OMFG this is what all the songs and poems are about this is IT!!” sometimes within the same encounter. It’s that way for every last human who has ever had a sexual encounter.*

Don’t worry about a checklist: “gotta do P in V, gotta do oral, gotta do this/that position.” YOU DON’T HAVE TO DO ANYTHING. Losing your virginity does not render you property or unable to say no to something. Any partner worth the term is there for fun and pleasure on behalf of both parties.

*By the by–referring to sex as a biological function in no way means I think it meaningless or mechanical or divided from morality. I don’t happen to believe in waiting until marriage/whatever (I didn’t by a long shot, but still call myself a nondom Christian), but if you do, that is a good and valid choice, as long as you don’t allow the choice to grow into an albatross around your neck.

My first time was three days after my seventeenth birthday, with the second guy I dated*, and while I loved the guy in question about as much as your average seventeen-year-old can love anyone romantically, I didn’t think we were forever, I didn’t question whether or not I was “ready”, and I went in with the expectation that the first time would be something to have out of the way.

And it was…rather pleasant, but a little painful at first–but honestly, if you’ve gotten a tetanus shot or had anything waxed or sliced your finger cutting onions, you’ve felt worse–and definitely awkward. And honestly? The GIQ was exactly what I needed when I was seventeen and a virgin…and not at all someone I could see dating two years later. So I’m a big fan of first-time sex not being with your One True Love or whatever.

Obvious notes: do have birth control, and a fairly definite plan (and some savings, one way or another) in case it fails, tell a friend where you’re going and why, blah blah blah.

And for the record: I, er, have a fair amount of sex, and I don’t think one partner’s as good as another–I’m actually fairly picky, because part of *having* had a fair amount of sex, for me, is knowing that the experience is nothing I can’t replicate pretty well with technology unless the particular guy pushes my buttons. So even if you go through with this and discover you actually dig casual sex, you don’t have to be up for it with the majority of guys.

*Honestly, I would’ve been willing to go there with my first boyfriend, but he was this uber-repressed kid from, I kid you not, Waco. And it’s probably just as well, considering how that relationship ended.

I was a late bloomer too – came very close at 21, but actually didn’t go all the way until 29…with little to no activity between the two. And now, at 38, I’m still single, and other than one three-year relationship, I have only basically had one night stands or very short term sex-only relationships. My problem is that I know I can have sex if I want to – I’m reasonably attractive and get a reasonable amount of attention on OkCupid – but it seems like all the guys that I find remotely interesting are only interested in sex and not in actually building a relationship. And I’m not that interested in the sex part – I want someone to hang out in my sweats and watch tv with…and then have sex later…

Which is basically to say, that even once you get the sex part out of the way, it doesn’t get much easier to navigate the relationship part of things. The best thing, IMO, is to work on being comfortable with yourself, sexually and non-sexually, and then to live your life in a way that makes you happy. And my recommendation around the getting turned on part – if you’re not a visual person (I relate), google free sex stories and peruse some of the written material that is out there – you can find just about variation that turns you on, you get some of ideas of what to do or not do, and hopefully enjoy yourself on your own either before diving in with someone else, or just when you need the release.

I don’t really have any advice, but also wanted to chime in and say you’re not alone. I can identify with pretty much everything you wrote.

I lost my virginity when I was 33 to someone I knew for about a year and haven’t seen since. I think “getting it over with” allowed me to focus on other issues instead of hyper-focusing on being a 30-something virgin.

I’ll have to come back and read the comments later, so apologies if this has been said.

Man, I am so there. I still haven’t had sex with anyone, and I’m embarrassed to go to my gynecologist and have her ask again, “well?” (It’s so she knows if she needs to check for HPV, not because she’s judgmental…but it’s still embarrassing.)

But I have used toys, which has helped me explore my body and open up my vagina so that it’s not so tight and painful. If you haven’t, then I would encourage you to. Start with a small dildo, not fancy, and play around with it. Work up to a larger and thicker ones, and see what your body can accommodate. Now, I’m sure it’s not the same…you can control the dildo, whereas a lover is harder to contain. But for me, it’s helped to reassure myself that I CAN insert something down there, all the way to the cervix, move it around vigorously, and just get used to how it feels. I’m much more confident now if/when it does happen, even though I know the actual experience will probably be much different. If nothing else, you’ll know what you like and don’t like.

And I just want to say a huge “thank you!” to Sarah, because intellectually, I know and agree that it is fine…but emotionally, it sure as hell doesn’t feel it. So I needed to hear it, and let myself not worry so much about it.

There’s nothing in your letter that talks about masturbation to orgasm. I’m going to guess that’s because you don’t. I’d really recommend changing that, and fast. If you are of the mind that sex should only be with somebody you love, well, isn’t that what masturbation is?

Check out some porn or erotica sites — you can do a search for lady-positive sites if the notion of ‘porn’ seems anti-lady to you. Written erotica might be a good safe start, so that you don’t further complicate things by comparing your body to the actors’. Cast a broad net, to see what-all out there arouses you. If you find something you like, go with it. Let it arouse you. Then go from there with your hand or toys. You’ll get used to what your arousal triggers are, and you’ll learn (by yourself! no judgy!) what floats your boat.

The more you know about your body’s responses, the less intimidating it will be to feel that way with another person.

I also second the rec for a professional sex worker. He’ll make it about you, and you’ll be able to get past yourself.

I’m 34 years old. I had my first actual kiss this year, with my second boyfriend (my first hung in there for 4 months with no kissing at all poor guy).

I had such a hang up about it, and I felt like an idiot, because who is 34 and yet to be kissed? I was in a very similar situation to you (never liked someone who liked me back — even that first boyfriend was more into it than me, which is why I didn’t want to kiss him — he is very nice though, in case you were wondering). So even though I was dating an INCREDIBLY patient guy who I really liked, I was anxious about anything physical. I worried about doing it right, about feeling comfortable, about being “good at it.” Finally he just asked if he could kiss me, I said yes, and he did, and it was a little awkward, but fine, and then it was less awkward, and then it was GLORIOUS, and I thought to myself, “why was I so worried about this?” I’m not at a sexin’ place yet, but I assume that will pretty much work the same way.

I don’t know what I’m offering here, except to say, Sars advice seems good to me, you’re not alone, and when things are in your head they end up seeming a lot bigger than they actually are.

While I had sex late in high school, I’m still happy I did it with somebody I liked and trusted but wasn’t in love with. He gave me a good experience and there was no crazy pressure to make it beautiful and perfect–in many ways, it’s good I didn’t fall in love at all until I was older. A situation like that might be good for you, but that’s your call. I will say that in my experience, male friends are really understanding and can give a very different perspective on sex from the stereotypical crap we see in the media. Thank goodness.

This, “I’m around men for a few months, gradually develop feelings for them, and then sexual attraction is the very last thing that happens.” IS TOTALLY ME. That’s not backward at all. I notice attractive people, but am not generally attracted to somebody until I get to know them, and that is kind of awesome actually. I hope you don’t feel like you’re wrong in this.

The only advice I have is for you to do things that make you feel better about yourself. If you love yourself, you will be more attractive and confident when the time for sex is right for you. I wish you the best.

You know, we live in the internet age. I haven’t googled, but I would bet my hat that there is a dating site or a sliver of a dating site for virgins to hook up with other virgins. Might be a lot of religion happening there, but it’s the internet! There has to be a whole gang of people out there in a similar boat, looking for similar things!

I gave up my v-card with a dude who was also a virgin. It was awkward and hilarious and even though we were both WAY too young, it took a lot of pressure off of both of us to realize that neither of us had any idea at all of how to do it with any kind of skill. I think if I’d been in a virge/non-virge combo I never would have gone for it because “what if I do it wrong and he laughs?” Real fear, that. And, like Sars said in an above comment, anyone who does that to you in bed is a giant douchecanoe and should be kicked out of your bed and then throw the bedside lamp at them.

So, perhaps you can use the power of the internet to find another virgin and get yourselves drunk (or get a hold of some er, recreational drugs), let those inhibitions go and go for it. It will be weird and awkward and maybe a little uncomfortable, but I promise you will be okay afterward.

Looks like I’ve got everyone else beat. I’m 42 and still a virgin. I’ve never been kissed, even. And I’ve definitely had the “Am I a big weirdo?” feelings. So I can relate to Conflicted.

In many ways, I could have written her letter. I’m also attracted more to personality than looks, and it takes me a while after I get to know someone to feel attracted to him. And it just doesn’t seem to happen that often, anyway.

Where I differ is feeling like I have to do something about it, like I have to make something happen just to get it done. I’ve decided if it happens, that’s great, and if it doesn’t EVER happen, well, that should be fine, too. What’s normal, anyway? Why should it be a big problem to be a virgin? It used to be considered shameful for a single woman to NOT be a virgin; is it now shameful to be one? I would hope that whether she decided to have sex now or not (and either choice would be fine), Conflicted would ultimately be able to feel content with herself and her life.

Whatever happens, hopefully Conflicted will feel a bit better after reading these replies from others who were/are in her situation. You are not alone.

I first had sex in my mid-twenties, which I considered ancient, and it was with someone attractive and kind whom I suspected would be good in bed and whom I knew wouldn’t fall madly in love with me or vice versa. I just wanted to have it over with.

He was kind, and he made it as good an experience as one’s first time can be. (It did hurt and there was awkwardness, but I think some of that’s inevitable.)

Afterward, I told him that he should be a king on some island where it’s the king’s job to deflower all the maidens.

Hey there Conflicted – welcome to the club that no one talks about existing!! It’s as if “first rule of Fight Club” was “don’t even admit to anyone else you might be in Fight Club”. I lost my virginity at the tender age of 36, to the guy I’m now engaged to. And I spent a lot of time before that majorly stressed out about the V-word – how do I bring it up, how do I just get it over with, should I settle for someone I don’t really want, etc.

And while I do kinda wish I had “gotten it over with” early on, by the time you hit your late 20s, you’re in a weird bind (or at least I was). By that point, and into my 30s, I felt like I was too old to be “stupid”, and too young to have completely given up on finding someone I really liked. And I felt really REALLY alone in that. But occasionally I would trust someone, usually a girlfriend, well enough to tell them about it (and I would almost always tear up because of the shame), and I discovered that in fact, not all of us lose our virginity on prom night. But pop culture doesn’t ever talk about that. If you’re a virgin over 25, you’re a joke on Seinfeld, or you’re clearly insanely religious and waiting for marriage. So it becomes really scary to bring this up to potential partners.

Here’s the thing I did “get over” – the shame of the v-word. I didn’t start announcing it on first dates or anything, but I did a couple of other things I think might be helpful.

A) I bought a vibrator. I actually bought a few. Someone’s already mentioned this, but getting more “in touch” (har) with the sexual side of myself without waiting for someone else to help out is what helped me get over the embarrassment at sexual stories or jokes that other people would tell.

B) I reviewed my sparse relationship history, and figured out that in most cases, I had been the one who chose to put on the brakes (in those cases where there was identified mutual attraction). Reframing my history as “I chose this” and not “they didn’t choose me” was helpful.

C) I had my own little “coming-out” moment – in a safe space, with a group of people I felt close to, I said the words “I’m a virgin.” Shaking the whole time. And people clapped, or gasped, or hugged me, but everyone was cool, and no one laughed. Which is really the big fear.

D) I found the most comfortable way for me to put myself “out there” – it might be online (I’m a big fan of OKCupid – it’s how I might my fella – and I know friends who are more hook-up oriented that use Adult Friend Finder), it might be finding social events that work for you. And just decide you’re going to meet people and see who you like and who you don’t – and maybe you’ll meet someone that you’ll eventually trust enough to tell them the short version of your story. For me, it was the trust that mattered, not a question of love – I lusted after plenty of dudes, but I’m marrying the guy that I trust without question.

This is way longer than I meant it to be, but know that you are not the only 35-year-old virgin out there. There are way more of you/us than anyone will ever talk about. And you’ll be just fine.

I would recommend some serious introspection (perhaps with the help of your therapist), to pick apart your motivations and make sure that you actually want to have sex and it’s not just societal pressure or cultural brainwashing or whatever the hell you want to call it. I haven’t had sex (going on thirty if anyone’s keeping virginal statistics), but I spent a fair amount of time assuming I wanted to because everbody else seems to want to. I’m certainly not trying to shove you into the asexual box here; if you want to have sex, then you want to have sex. But the reasons you list seem more along the lines of outside entities making you feel like you ought to have sex, which is [ideally] not how it should work.

Absolutely seconding what sb said – I was going to link to the AVEN site, and mention demisexuality in particular.

I’m another “lost my virginity in my early 20s to get it over with” and I certainly don’t regret it, despite the sex not being the greatest, because the curiosity would have killed me eventually.

But the best decisions I’ve made about my sex life have been: a) buying a vibrator. More than one. Many, in fact; and b) educating myself about my sexuality. I’m so much more relaxed about my lack of partners since I realised I’m homoromantic, but (mostly) heterosexual. I have deeply satisfying emotional relationships with women, and many, many orgasms (mostly solo, very occasionally with men), and it all takes up much less mental real estate than it used to. Labels aren’t for everyone, but I underestimated how much it would help to have some fancy terms to pull out at dinner parties where I’m the only person at the table not Smug Married. My non-tradional sexuality does not need your pity, thanks.

Check out Hank Green’s Sexuality if Complicated video on youtube for a simple, clear introduction to the topic.

To those who recommend sex workers: it’s my understanding that male heterosexual sex workers are very few and far between. Gay male sex workers and straight female sex workers abound, but straight male sex workers are pretty rare (I have no idea about gay female sex workers). I think you can find bi male sex workers a bit more easily; correct me if I’m wrong. (And if Showtime’s Gigolos is to be believed, straight male sex workers are kind of busted.)

However, going the casual/one-night stand route is fine. I lost mine at 18 to a guy I’d been out with a few times and didn’t really see much after we had sex. I’ve had other one-night stands and casual relationships, and it’s simply a different kind of fulfilling than in-love sex – it’s like junk food.

It strikes me that the LW mentions attraction but not masturbation; if that’s not a part of her sex life, I would highly recommend some self-exploration. Everyone should know what makes them feel good.

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I don’t have any advice that hasn’t been mentioned already, but I was extremely nervous about being a virgin when I got married at almost 30. My fiance had been married before, and I was certain that I was going to be a disaster. In my mind, it was SEX!!!?!?!#^@)$*$&#*~!!!

I also recommend self-exploration; order some fun stuff from Amazon.com! Knowing what my body liked gave me confidence, and my husband was delighted that I was up for an adventure.

On a practical note, if you decide to “give him your flower” (ala Monica on Friends), preparing a little basket of necessities (lube, small towel, massage oil, electronics, protection, etc) to keep in your bedside table might help you get in the mood mentally as you look forward to whatever is to come.

I enthusiastically second Sars suggestion to just do it. It was a great decision for me at least. With someone I liked, and still like as a friend, who is kind and smart and totally onboard with condom use.

Over-thinking is one of the least helpful things you can do regarding sex. Being smart and careful is important, of course, but once the practical bases are covered, letting go and going for it almost always works out okay.

Like ferretrick said, we don’t know you, but . . . are you absolutely, positively, 100% sure that it’s a guy you need? Because, I’m serious here, what you’ve said sounds like what some late-to-figure-it-out lady-lovers I’ve known have said. From my perspective (which was from high school), I thought making out with guys was, well, nice and sometimes even a bit arousing, but once I first kissed a girl — I knew that was it. If you are sure, that’s great, I just wanted to add another voice to say that you should make sure that you’re sure. (Sorry, Sars, I’m not eloquent tonight.)

44 here, people, and perfectly fine with this for myself. Just don’t want to anything that under circumstances that would leave me feeling guilty, stressed, or regretful. Until the right situation arrives, I have other things to do. Works for me.

From the letter, it didn’t sound like you have ever told anyone this. You might consider talking to a friend, if you have even one friend who has shown s/he is not gossipy. I don’t know how far away your friends are, so maybe it’s too difficult for you to get together with one of them (or maybe it would be easier on the phone?). But if you can, just say, “I need to talk to you about something that is private and I don’t want you to repeat it to anyone else, but I really need to get it off my chest. *deep breath* You know the guy in The 40-Year-Old Virgin? Well, that’s me.”

My best friend is 37 and still a virgin, and doesn’t care whether she ever has sex, and it seriously makes no difference to me. Obviously I don’t know your friends, but I would hope to God that they would say nothing worse than, “Well, it does bother me that you felt you had to lie about sex to make me like you.”

It’s entirely possible your friend will say, “Well, sure, you’re unusual, but QUIT CALLING YOURSELF AN ABNORMAL FREAK.” It’s even possible your friend will tell you that her boyfriend’s friend is on the rebound, and was saying he wished he could have a night of no-strings-attached guilty-pleasure sex to get over his ex, and he’s a pretty nice guy, so why don’t we invite him over for a drink, and if you like him we’ll announce that we are suddenly tired and are going to bed, and you and he can sit on the pull-out couch and have a few more drinks… I know someone who actually did this for a friend, when she learned that the friend hadn’t had sex in 7 years and was upset and embarrassed about it. Good friends are going to love you, and want you to be happy, and want to help you. Even if it means they have to buy a slipcover for their couch.

I don’t really have any advice for you but I’m so glad you wrote this letter, Conflicted. Reading all the comments from other 30+ v-card carriers makes me feel like less of a freak.

I don’t know how I ended up here! The most ridiculous part is that I was in a live-in relationship for many years so I doubt anyone I know would ever guess that I’m still technically a virgin. We got together when I was pretty young and, having grown up in a religious household, at that time I bought into all that saving-myself-for-marriage stuff. We did other things (rounded all the bases but never made it all the way home) but never the Big One. And then our relationship slowly fizzled into a straight-couple version of lesbian bed death, and we were basically roommates who pretended to be a couple. At a certain point I realized I didn’t care about saving myself for marriage anymore, but that ship had sailed in that relationship. In retrospect it was incredibly stupid to stick with it for so long, but we were great friends and didn’t want to let go.

Soooo here I am, 32, and I’ve never had sex. I don’t have any hot prospects. I am terrible at meeting new people and I don’t have any single guy-friends to try a friends with benefits situation. I have zero recent dating experience and no clue how to even initiate a one night stand.

I assume it will eventually happen but I’m pretty embarrassed about it. I waver back and forth about whether I will tell the person when the time comes. I guess I’ll decide based on whether it’s a guy I really want to have a relationship with (tell) or a more casual thing (don’t tell).

Anyway, I just wanted to chime in that there’s one more person like you out here, dealing with the same issue.

With respect, @No Name for This One, no form of birth control is ever 100%, but with the proper precautions the risk of STDs or pregnancy is very very low. Life is risk, yo. Waiting for a 100% situation will get you laid exactly never. It’s for the LW to decide what degree of risk she wants to take, but all of us have to take some risk in order to hook up.

@Flick, you’ve had some great and sensitive advice here. I’d strongly echo those who encouraged you to masturbate and figure out what turns you on – you don’t need to pressure yourself to come at first if you’re unaccustomed to that, just think about what feels good. Also, when you do come to do it (either masturbate or sexing): make sure you’ve got lube. It can help ease discomfort and take the pressure off, especially if you find you’re not strongly aroused at first.

Yup, I’m there too – 38 and still tagged with a V. I’ve fooled around a bit, and enjoyed it, but none of my very few relationships lasted long enough for me to be comfortable with Going All the Way (we’re talking three or four months, tops). I’ve just never liked the idea of having sex with someone I wasn’t at least reasonably attracted to, and I’m just not attracted that often. That description of “demisexual” posted by sb looks awfully familiar…

On the one hand, I’m personally disappointed – not entirely for societal reasons: I’ve always kind of wanted kids, for one thing, and that’s looking less and less likely (though I have nothing against adoption). Also, I have enjoyed the fun I’ve had when I’ve had it, but despite experimentation, haven’t quite figured out how to enjoy it on my own. On the other, I have a lot of friends from a lot of different parts of my life; I’ve recently switched careers entirely from one I loved to one I’m loving in an entirely different way; if the rest of my life is at least as good as this I won’t die unhappy in fifty years or whenever.